Breaking the Inside
by emebalia
Summary: In Hell Alastair comes up with a new way to torture Dean. Very dark. WARNINGS inside.


**A/N** This is entirely lilykep's fault.

**Warnings:** Torture, gore, body horror, non-con, bestiality, tentacle rape

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**Breaking the Inside**

His first day in Hell Dean tried to keep his fuck-you-attitude. He knew pain, he knew how to deal with pain. He thought he was prepared. Turned out he wasn't.

His attitude dissolved in blood and pain what felt like an eternity later but probably wasn't more than half an hour. Maybe. As if time mattered in Hell.

Dean still counted the days. From his first day when he'd first met Alastair – who'd introduced himself as Hell's torturer number one and who'd driven that point home with the razor he was so fond of leaving Dean as a bubbling mess of incoherent flesh – to day one-hundred, one-thousand, five-thousand and so on. Why he counted the days Dean had no idea, those were only landmarks on his way down the road to eternity. This would go on forever. Today, tomorrow, a million years from now and still no end in sight. Because there was no end. Even if he finally broke – and Dean had no doubt that at some point he would break, everybody broke sooner or later – it wouldn't end. It would shift. From one kind of torture to another one. And he wasn't sure which one was worse.

A long time ago when he'd been alive and still had known what the sun felt on his skin a demon had told him that Hell was Hell even for demons. Back then he'd not believed her. Back then his mind couldn't imagine, couldn't understand what Hell was. Now he knew.

And still he counted the days as if they mattered. As if it mattered in the end if he'd lasted three days or three-thousand. Okay, he had already passed that mark so it would probably take thirty-thousand or three-million days but in the end it didn't matter. He would break.

The only thing that came close to being not bad, not agonizing hot pain, was the fact that over time Alastair became more frustrated. Almost desperate.

Dean was that stupid little toy that refused to break and Dean drew something out of that fact. Power, strength, hope. As if those things existed in the Pit.

However, desperate Alistair led to creative Alistair. The razor was still his weapon of choice but he let his mind run wild and came up with some pretty fucked up ways to torture Dean.

Dean had expected to get raped in Hell – it was an easy, run-of-the-mill way to fuck up people after all – and for sure it was among the first things Alastair did to him. No surprise there. He didn't do it that often, Alastair was more a carver than a fucker, and when he did it, he liked to bring his razor in for the play. In the end it was just another way to get ripped apart.

"Thought we'd do something special today." Alastair stood over him, razor in hand and a smile on his lips.

"Did I miss your birthday?" Dean croaked out. His throat was dry but soon enough he'd taste his own blood, he knew that. He lay spread-eagled on the rack, thick leather cuffs holding him in place, his body strung up tight enough for him to feel the strain in his muscles and joints. Except for a thin layer of sweat he was naked, clothes were optional at best in Hell. At least it was warm enough to go without. An eternity ago Dean would have laughed about this joke.

"I got a new pet." Alastair sounded excited so it maybe was his birthday.

"Should I get jealous?" Dean licked his dry lips, dreadful anticipation building up in his guts. However, as long as Alastair kept talking said guts stayed inside his body and Dean was grateful for every breather he got. Every second counted.

"Don't worry, you're going to be best friends." Alastair stepped around the rack, out of Dean's view where he kept his more interesting tools, and Dean fought the urge to crane his neck. He wouldn't see much anyway and if Alastair caught him doing that he'd just cut the tendons in his neck with a disappointed _tsk tsk tsk_. Been there done that. Dean wasn't supposed to spoil the surprise. It was never a good one anyway.

A second later Alastair was back at his side with a small glass tank. Thick glass held together by welded iron bands and when Alastair set it on the table next to the rack with a thud Dean thought he saw something moving in the murky water inside.

This wasn't good, Dean knew that while a distant part of his brain wondered where Alastair had found water in Hell.

"What's in the box?" Dean's mouth formed the words and he was pretty sure there was a funny meaning behind them but if there was it was long lost, burned to crisps in hellfire.

Alastair opened the heavy latch. That latch alone told Dean that whatever was inside better stayed inside but Alastair had other ideas. He didn't hesitate and reached with both hands inside. Through the glass Dean saw his hand moving in the murky water and something swirled around his wrist.

When Alastair lifted that thing out of the tank, slimy water dripped in thick ropes from his hands.

Dean squirmed in his bindings but strung tight like he was he couldn't move at all so he just watched with wide eyes while Alastair placed that thing on his stomach. Dean flinched at the sudden cool sensation, slime dripping down his sides and between his legs.

The thing had roughly the size of a basketball and a grayish color under all that snot and for a second Dean thought it wasn't that bad.

Then that thing unfolded itself. Like it had to stretch after being stuffed in that tiny tank the thing uncurled its appendices until it lay spread out on Dean's stomach, tentacles flowing all over him, tickling his sides, the hollow of his neck and a few very unpleasant ones had found their way between his legs.

"A squid?" Dean breathed out a humorless laugh. "You have to be fucking kidding me."

"You're right about the fucking part." Dean didn't dare to tear his eyes off the squirming mess but he didn't have to look at Alastair to know what expression he was wearing right now. A smug grin like he was very pleased with himself which he probably was.

"Tentacle porn? Never tried that one." Dean tried to hide his horror but the way Alastair chuckled he failed.

As far as Dean could tell the creature consisted of a more or less round body and what looked like a million tentacles. It had no eyes or any other sensory organs that Dean could see and at first the tentacles crawled rather aimlessly over his body.

One brushed his right nipple by accident and Dean flinched, more out of surprise than anything else but it was enough to get that thing's attention. The tentacle, which had already moved on, was back in a heartbeat and latched itself on the nipple.

"Fuck!" Sharp pain pierced through Dean's chest while the suckered underside of the tentacle dug itself deeper into the sensitive flesh.

Encouraged by his reaction the thing became eager. A second later another tentacle had found the other nipple and latched on to it like leech.

Dean threw his head back, eyes screwed shut, biting his lips, the only movements the bindings allowed him, but with that he bared his throat to the creature.

He gasped first in surprise and then for air when a tentacle found its way around his neck. Another one used the opportunity to slip inside his mouth. The smell and the bitter tang of the slime made him gag.

He didn't surrender that easily, though. Dean bit down. Hard.

The creature made a bristling noise and Dean felt a little spark of triumph.

It answered with biting his nipples and tightening around his neck. Dean let go of the fleshy thing in his mouth in a breathless scream and more tentacles found their way in his mouth.

Others went more south. Dean felt them on his legs, inner thighs and crawling over his flaccid cock. It shriveled even more under the tough as if his junk tried to retreat into his body.

One curled around his balls and another one around the base of his cock. Or it was the same one, Dean had lost count of how many of them were down there. They squeezed and sucked and swirled, flooding him with sensation. He hated to admit it, it kinda felt good.

It did, however, surprise him how long it took for one of them to find his hole. First it slipped up and down between his ass-cheeks, almost gentle, before the blunt tip wormed its way into his body. Dean tensed at the intrusion but the tentacle just worked through the tight muscles.

For a moment everything fell into a rhythm. That squid thing worked his mouth, ass and cock with matching movements, stroking him to full hardness while the others fucked him from both ends. The one in his ass even managed to hit his prostate more often than not and by now Dean wasn't fighting the tentacle beast anymore he was fighting a losing battle against his building orgasm.

"I knew you'd like each other." Alastair commented, clearly aware of Dean's silly little fight. He always took pleasure in making Dean come.

Dean wanted to snarl at him but with tentacles slipping in and out of his mouth he couldn't even breathe properly. It didn't help that the one around his neck squeezed in rhythm with the others, leaving Dean light-headed and on the edge of suffocation.

The orgasm ripped through him like an inexorable force. Dean would have screamed if he could. The tentacles milked his cock, squeezed his balls, wringing every last drop of come out of him.

When Dean came down from his orgasm, he hoped that was it. Alastair had gotten what he wanted.

"And you always say I never do something nice to you." Alastair mused while the creature just kept going.

Dean's cock was sensitive now, the touch borderline to painful but the tentacles curled around it didn't care. They kept on moving.

A second one forced its way into his asshole, both now alternating fucking into him, and Dean tried to breathe against he pain of being stretched like this. However, breathing had been an issue for a while now and Dean struggled against the rising panic.

In all those years his body had never really grasped the fact that this was Hell. He was already dead, this body was just an illusion, he couldn't die from suffocation or blood loss or anything. No matter how much he sometimes, always, wished he could.

So when another tentacle forced its way in his mouth, breaking open his jaws, ripping the corners of his mouth into what was just the beginning of a Cheshire grin, Dean's lungs burned in need for oxygen and he choked on the slimy mess in the fruitless attempt to breathe.

Then his groin exploded in hot agony.

"Nasty little suckers." Dean heard Alastair's comment through the red mist of pain but the words didn't make sense. "You weren't that attached to your balls anyway, right?"

More tentacles forced their way into his body, working their way down his throat and deeper into his ass. They tore their way in, tissue ripped apart and blood rushed out of Dean's body like water.

Dean felt them moving inside him, reaching for each other when both sides came closer to his middle.

He felt them coming together in his stomach, curling into a giant knot. The ones still outside his body tried to join the reunion and some took the easy route and just dug new holes in his chest and stomach.

This was Hell so the agony never stopped and Dean could never flee into unconsciousness. His brain still registered the flaring pain of being gutted alive.

"Look at this." Alastair gently lifted Dean's head so he could see. "Isn't it cute?"

The squid sat happily purring in what had been Dean's body. Tentacles curled around the remains of Dean's organs.

"Let's do this again tomorrow, shall we?" Alastair dropped Dean's head and moved around to look him in the eye. "Unless you don't want to. You know, you could get off this rack in a heartbeat. What do you say? Just give me one nod and this is all over."

Alastair's smile was charming and Dean wanted to give in. He wanted to give in so badly but he didn't. Not today.

Instead he told Alistair to stick it where the sun don't shine. Or at least he would have. If he wasn't missing his lower jaw right now.

"No?" Alastair sounded disappointed. "Oh well, maybe tomorrow."


End file.
